The 9-decalyl and related cations. I. Generation of the 9-decalyl cation by solvolysis

Abstract

Kinetic and product studies have established that π-bond participation occurs in the acetolysis of 4-(cyclohex-1-enyl)but-1-yl derivatives to give a 9-decalyl cation. Quantitative analyses of the mixtures of products formed by the x-route (from 4-(cyclohex-1-enyl)but-1-yl derivatives), π-route (from spiro[4,5]dec-6-yl derivatives), and direct routes (from cis- and trans-9-decalyl derivatives) show that the intermediate 9-decalyl cations generated in each case must be different. Reasons for the differences are discussed; it is suggested that the counter-ion in ion-pairs involving cis-like and trans-like conformers of the 9-decalyl cation probably plays an important role in product formation.